Chester Hotel Guide - 4 Stars Hotels in Chester, Vermont

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Tonight
22 Apr - 23 Apr
Tomorrow
23 Apr - 24 Apr
This weekend
24 Apr - 26 Apr
Next weekend
1 May - 3 May

Our top choices for Chester 4-star hotels

Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (572 reviews)
"Amazing restaurant and attentive staff"
United States
Noelle
The price is Rp5.297.187
Rp6.581.196 total
includes taxes & fees
28 Apr - 29 Apr
Woodstock Inn & Resort
House (Meadow) | View from room

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (613 reviews)
"Accommodations were tires Breakfast staff was surly "
United States
Andreas
The price is Rp1.621.477
Rp2.703.207 total
includes taxes & fees
10 May - 11 May
The Equinox Golf Resort & Spa
Meeting facility

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
4.0 star property
Manchester Village Historic District
9.4 out of 10, Exceptional, (837 reviews)
"Best atmosphere and family stay ever. Kids friendly."
United States
Simona
The price is Rp2.760.023
Rp3.696.031 total
includes taxes & fees
29 Apr - 30 Apr
Kimpton Taconic Hotel by IHG
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,004 reviews)
"Had a lovely stay while visiting, enjoyed the breakfast and the staff were all very friendly and accommodating. Would def stay here again"
United States
dylan
The price is Rp2.680.137
Rp3.576.716 total
includes taxes & fees
27 Apr - 28 Apr
On The River Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (278 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is Rp2.558.593
Rp2.814.366 total
includes taxes & fees
20 May - 21 May
The Jackson
American cuisine

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
4.0 star property
Manchester Village Historic District
9.8 out of 10, Exceptional, (360 reviews)
"Great stay, the lodge room was spacious and spotless with a huge bathroom and fireplace. Food in the restaurant was excellent. Would stay there again. "
United States
Laurie
The price is Rp3.411.457
Rp3.752.603 total
includes taxes & fees
27 Apr - 28 Apr
The Reluctant Panther Inn and Restaurant
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (29 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is Rp2.237.161
Rp2.438.506 total
includes taxes & fees
29 Apr - 30 Apr
Four Columns Inn
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (79 reviews)
"Great location, service and restaurant "
United States
LUDJANE
The price is Rp3.037.911
Rp3.942.185 total
includes taxes & fees
5 May - 6 May
The Inn at Weathersfield
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very good, (40 reviews)
"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."
United States
J
The price is Rp3.190.673
Rp3.477.893 total
includes taxes & fees
4 May - 5 May
Windham Hill Inn
Exterior

Seesaw's Lodge

Seesaw's Lodge
4.0 star property
Peru
10.0 out of 10, Exceptional, (26 reviews)
"Great cabin with an even greater staff!!"
United States
Eyasser
The price is Rp3.295.571
Rp3.592.172 total
includes taxes & fees
30 Apr - 1 May
Seesaw's Lodge
Restaurant

The Hermitage Inn Vermont

The Hermitage Inn Vermont
4.0 star property
West Dover
8.8 out of 10, Excellent, (18 reviews)
"Wonderful stay at the Carriage House! Beautiful property and excellent amenities! Perfect winter getaway! "
United States
Caroline
The price is Rp5.515.760
Rp6.067.422 total
includes taxes & fees
4 May - 5 May
The Hermitage Inn Vermont
Front of property – evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
The price is Rp5.162.443
Rp5.601.304 total
includes taxes & fees
27 Apr - 28 Apr
Chesterfield Inn
Exterior

Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts
4.0 star property
Clock Tower Base Area
7.8 out of 10, Good, (35 reviews)
"Great location!"
United States
DIEN
Solitude Village at Okemo by Vail Resorts
Terrace/patio

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (96 reviews)
"Inn was beautiful, the details exactly what you'd want for a weekend getaway. Room was cozy (room 6), bed was comfortable, jetted tub was awesome for us not having a tub at home, bar was a nice place to hang out and breakfast was excellent. Location was perfect, it was an easy walk into the center of town, even in winter. Honestly, nothing bad to say."
United States
Nicholas
The Village Inn of Woodstock
Exterior

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The Woodstocker B&B
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is Rp4.278.036
Rp4.705.925 total
includes taxes & fees
27 Apr - 28 Apr
Inn on Putney Road
Property grounds

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property
4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (26 reviews)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo, A Vail Resorts Property
Apartment (3 Bedrooms) | Interior

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
4.0 star property
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful four night stay at this great condo! Perfect if you are skiing out of Okemo! The condo was beautiful, clean and the host Bill was so communicative and responded to texts immediately. The gym and spa was also an added bonus! Great time! "
United States
Nipa
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Apartment (2 Bedrooms) | Interior

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
4.0 star property
West Dover
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
Apartment (2 Bedrooms) | Interior

Updated Vintage Apartment < 1/2 Mi to Main St

Updated Vintage Apartment < 1/2 Mi to Main St
4.0 star property
Keene
Updated Vintage Apartment < 1/2 Mi to Main St
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester.
The Weston

The Weston

630 Main St Weston VT
The price is Rp5.571.475 per night from 23 Apr to 24 Apr
Rp5.571.475
Rp6.072.908 total
23 Apr - 24 Apr
includes taxes & fees
10/10 Exceptional! (9 reviews)
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester
aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

On The River Inn

On The River Inn

8/10 Good
"Clean room, friendly staff, family-friendly. "
Suwei 1-night trip
Posted 4 hours ago
On The River Inn

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
With Expedia's sort and search filters, scoring a terrific deal on a 4-star hotel in Chester just got simpler. Start by keying in your chosen arrival date and length of your holiday. Then list the results by price and choose a property that best fits your style and budget.

  • Search for the lowest price from Rp6.072.908

What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveller experience and upscale décor, 4-star hotels are an excellent option for your Chester break. These kinds of accommodation generally come with loads of handy amenities that make it a breeze to unpack and unwind — think complimentary bathrobes, gyms and pools. Or live the high life at a 5-star hotel designed to indulge you in luxury perks and amenities. On-site health clubs, oversized bathrooms and gourmet dining are typically featured at these deluxe retreats.
Does Chester have any 4-star all-inclusive resorts?
Finding holiday bliss in Chester is as easy as entering in your dates and selecting our "All inclusive" filter. Stay and play where almost everything is already taken care of like your meals, accommodation, entertainment and activities, or opt for a standard 4-star resort in or around this top destination.